EP1565164A2 - Gels phospholipidiques se formant d'eux-memes - Google Patents

Gels phospholipidiques se formant d'eux-memes

Info

Publication number
EP1565164A2
EP1565164A2 EP03788818A EP03788818A EP1565164A2 EP 1565164 A2 EP1565164 A2 EP 1565164A2 EP 03788818 A EP03788818 A EP 03788818A EP 03788818 A EP03788818 A EP 03788818A EP 1565164 A2 EP1565164 A2 EP 1565164A2
Authority
EP
European Patent Office
Prior art keywords
phospholipid
gel according
phospholipid gel
antibiotic
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP03788818A
Other languages
German (de)
English (en)
Other versions
EP1565164B1 (fr
Inventor
Julia Eva Diederichs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MCS Micro Carrier Systems GmbH
Original Assignee
MCS Micro Carrier Systems GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by MCS Micro Carrier Systems GmbH filed Critical MCS Micro Carrier Systems GmbH
Publication of EP1565164A2 publication Critical patent/EP1565164A2/fr
Application granted granted Critical
Publication of EP1565164B1 publication Critical patent/EP1565164B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants

Definitions

  • the invention relates to self-forming gels consisting of natural, semi-synthetic and synthetic phospholipids and water.
  • the gels can be used for the moisturizing or calming treatment of the skin, mucous membrane, natural or surgically produced body cavities, or contain pharmacologically active substances which are released on or into the skin, mucous membrane, natural or surgically produced body cavities or compartments.
  • the gels can be added as a stabilizer or solubilizer to pharmaceutical formulations.
  • Phospholipids are used in the form of liposomes as topical excipients. [Schreier & Bouwstra, J. Control. Release 30, 1-15, 1994; Cevc, Crit. Rev. Ther. Drug carrier system. 13, 257-288, 1996; Yarosh, Photodermatol. Photoimmunol. Photomed. 17, 203-212, 2001] and as components of cosmetic preparations such as creams and lotions [Weiner et al., J. Drug Target. 2, 405-410, 1994].
  • Liposomes are usually used directly in their aqueous, disperse form or incorporated into a gel-forming matrix including pharmaceutically used base creams or hydrogels.
  • Ghyczy and co-workers describe an alcoholic phospholipid gel with a phospholipid content of 15-30% and 14-20% alcohol. Brandl and co-workers have developed and characterized three-dimensional liposome networks from highly concentrated (60%) semi-solid phospholipid dispersions. [Brandl et al., Adv. Drug Deliv. Rev. 24, 161-164, 1997; Brandl et al., Chem. Phys. Lipids 87, 65-72, 1997; Brandl et al. US 6,399,094]. Vesicular phospholipid
  • Gels consisting of 40% phosphatidylcholine and cholesterol have been used as carriers for cytostatic agents for the local treatment of cancer [Moog et al., J. Liposome Res. 8, 87-88, 1998; Güthlein et al., J. Liposome Res. 10, 251-252, 2000; Unger et al., WO 99/49716].
  • Ibscher Dissertation, University of Freiburg, Germany, 2000; Ibscher & Fridrich, WO 01/13887 A2] developed a phospholipid gel as a topical carrier for antiviral treatment. skin action consisting of phospholipids, alcohols and sugar alcohols or carbohydrates.
  • ethosomes Vesicular systems consisting of a low phospholipid (2%) and a high alcohol content (30%), so-called ethosomes, have also been described for topical use and for the transport of active substances into the skin [Touitou et al., J. Control. Release 3, 403-418, 2000; Dayan & Touitou, Biomaterials 21, 1879-1885,
  • the present invention relates to a phospholipid gel consisting of a neutral and a negatively charged phospholipid and water.
  • the phospholipids used in the gels of the present invention can be selected from natural, semisynthetic or synthetic phospholipids.
  • the phospholipids used according to the invention can be selected from natural, semisynthetic and synthetic phospholipids.
  • Suitable phospholipids that can be used in the phospholipid gel according to the invention are, for example, phosphatidylcholines.
  • natural neutral phospholipids are soy phosphatidylcholine and egg phosphatidylcholine.
  • Any fatty alkanoylphosphatidylcholines, in particular those derived from saturated or unsaturated C 8 -C 22 -alkanoylphosphatidylcholines, can be used as synthetic or semi-synthetic phospholipids.
  • the fatty alkanoyl residues are derived, for example, from caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachic acid, behenic acid, oleic acid, tubercolostolic acid, Linoleic acid, linolenic acid, elaeostearic acid, arachidonic acid, clupanodonic acid, docosahexaenoic acid and any mixtures thereof.
  • a preferred phosphatidylcholine is dipalmitoylphosphatidylcholine.
  • Negatively charged phospholipids are in particular those which contain a residue of an acid salt in the molecule.
  • negatively charged phospholipids are, for example, phosphatidylglycerol, which is one of the naturally occurring negatively charged phospholipids.
  • Further examples are dialkanoylphosphatidylglycerols, the alkanoyl radical being able to be derived from the above-mentioned fatty acids. Dipalmitoylphosphatidylglycerol and dimyrrestoylphosphatidylglycerol can be mentioned as examples of suitable dialkanoylphosphatidylglycerols.
  • negatively charged phospholipids are phosphatidylserine and phosphatidic acid, each of which may also contain fatty acid chains in the molecule, the fatty acid chains here also being able to be derived from the above-mentioned fatty acids, such as, for example, from palmitic acid.
  • Another negatively charged phospholipid is, for example, phosphatidylinositol.
  • the negatively charged phospholipids preferably have alkali ions or ammonium ions as the cationic counterion. The choice of the cation is not limited to certain cations, provided that these are physiologically compatible.
  • the total phospholipid concentration is preferably in a range between 6 and 40% by weight.
  • the ratio of neutral phospholipid to negatively charged phospholipid can be selected in a wide range, preferably the ratio of neutral phospholipid to negatively charged phospholipid is in the range from 10: 0.01 to 10: 5, in particular from 10: 1 to 10: 0, 25th
  • any pharmacologically active substances can be incorporated into the phospholipid gel according to the invention.
  • the active substance are steroids, non-steroidal anti-inflammatory drugs, antibiotics, antioxidants, or anti-epileptics.
  • the steroids can, for example, be selected from the group consisting of hydrocortisone or dexamathasone
  • the non-steroidal anti-inflammatory drug is selected from the group consisting of ibuprofen, diclofenac, flurbiprofen or nabumetone
  • the antibiotic is selected from the group consisting of tetracycline or one of its Derivatives, an aminoglycoside such as gentamycin or neomycin, a macrolide antibiotic such as erythromycin, a nitroimidazole derivative such as metronidazole or flucidic acid, an antibiotic peptide or an antibiotic oligonucleotide
  • the antioxidant is selected from the group consisting of vitamin E or coenzyme Q 10
  • Phosphatidylcholine and Phosphatidylglycerol called.
  • This can be done, for example, with the natural components soy phosphatidylcholine and phosphatidylglycerol, but also with mixtures of synthetic phosphatidylcholine / phosphatiylglycerol such as dipalmitoylphosphatidylcholine and dipalmitoylphosphatidylglycerol or dimyristoylphosphatidylglycerol.
  • the gel forms spontaneously from a thin lipid film when it is dispersed in water with gentle shaking.
  • Dispersion under high shear and high pressure is not necessary.
  • Organic solvents, detergents or bridging divalent ions are also not necessary.
  • Active substances can be incorporated into the gel; in particular substances of the ubiquinone type such as coenzyme Q 10 can be present without interfering with the formation and stability of the gel structure.
  • 1A 180 mg soy phosphatidylcholine and 20 mg egg phosphatidylglycerol are deposited as a thin film on a glass wall. 1 ml of distilled water is added and the container is shaken on a shaker at low speed until a gel has formed. The gel is transferred to a syringe and stored at 4 ° C.
  • 1D The same process is carried out to form a gel of 90 mg phosphatidylcholine and 10 mg phosphatidylglycerol.
  • 2A 150 mg dipalmitoylphosphatidylcholine and 15 mg dimyristoylphosphatidylglycerol are deposited as a thin film on a glass wall. 1 ml of distilled water is added and the container is shaken on a shaker at low speed until a gel has formed. The gel is transferred to a syringe and stored at 4 ° C
  • Example 3 180 mg of dipalmitoylphosphatidylcholine and 20 mg of dimyristoylphosphatidylglycerol are mixed with

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pain & Pain Management (AREA)
  • Toxicology (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Il a été constaté, de manière surprenante, qu'au contraire d'autres systèmes, des phospholipides neutres et négativement chargés forment spontanément un gel lorsqu'ils sont ajoutés à de l'eau. Ce gel est suffisamment stable pour être utilisé, plus précisément par ex. pour remplir des récipients ou des seringues, et pour être appliqué sur la peau humaine ou sur des parties du corps.
EP03788818A 2002-11-26 2003-11-24 Gels phospholipidiques se formant d'eux-memes Expired - Lifetime EP1565164B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10255285A DE10255285A1 (de) 2002-11-26 2002-11-26 Selbst formende Phospholipid-Gele
DE10255285 2002-11-26
PCT/DE2003/003883 WO2004047790A2 (fr) 2002-11-26 2003-11-24 Gels phospholipidiques se formant d'eux-mêmes

Publications (2)

Publication Number Publication Date
EP1565164A2 true EP1565164A2 (fr) 2005-08-24
EP1565164B1 EP1565164B1 (fr) 2012-10-24

Family

ID=32240469

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03788818A Expired - Lifetime EP1565164B1 (fr) 2002-11-26 2003-11-24 Gels phospholipidiques se formant d'eux-memes

Country Status (6)

Country Link
US (2) US20060039978A1 (fr)
EP (1) EP1565164B1 (fr)
JP (1) JP2006508990A (fr)
AU (1) AU2003292983A1 (fr)
DE (1) DE10255285A1 (fr)
WO (1) WO2004047790A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018172504A1 (fr) 2017-03-23 2018-09-27 Lipid Systems Sp. Z.O.O. Encapsulation à haut rendement de composés hydrophiles dans des liposomes unilamellaires

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DE19633169A1 (de) 1996-08-17 1998-02-19 Teves Gmbh Alfred Elektromotor-/Pumpenaggregat
US8808715B1 (en) * 2004-11-23 2014-08-19 Georgia Regents Research Institute, Inc Methods and compositions for modulating keratinocyte function
EP1674081A1 (fr) 2004-12-23 2006-06-28 KTB Tumorforschungsgesellschaft mbH Préparation de nano-particules à bases lipides en utilisant une centrifuge duale et asymétrique
JP5523652B2 (ja) * 2006-06-27 2014-06-18 クラシエホームプロダクツ株式会社 ゲル状化粧料及びその製造方法
WO2011075623A1 (fr) 2009-12-18 2011-06-23 Latitude Pharmaceuticals, Inc. Composition de gel à une phase comprenant des phospholipides
CN103705442B (zh) * 2012-09-28 2017-12-01 上海恒瑞医药有限公司 原位脂质凝胶药物制剂及其制备方法和用途
CN103705439B (zh) * 2012-09-28 2017-11-28 上海恒瑞医药有限公司 脂质凝胶药物制剂及其制备方法和用途

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018172504A1 (fr) 2017-03-23 2018-09-27 Lipid Systems Sp. Z.O.O. Encapsulation à haut rendement de composés hydrophiles dans des liposomes unilamellaires

Also Published As

Publication number Publication date
US20120009169A1 (en) 2012-01-12
US20060039978A1 (en) 2006-02-23
WO2004047790A3 (fr) 2004-09-30
EP1565164B1 (fr) 2012-10-24
AU2003292983A8 (en) 2004-06-18
JP2006508990A (ja) 2006-03-16
DE10255285A1 (de) 2004-06-03
WO2004047790A2 (fr) 2004-06-10
AU2003292983A1 (en) 2004-06-18

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